Non-enzymatic electrochemical sensor for measuring analytes

Abstract

Embodiments described herein relate generally to compositions that include a synthetic redox-active receptor, and in particular to compositions that include a boronic acid based synthetic redox-active receptor which can electrochemically sense a target analyte in a sample solution. In some embodiments, a synthetic redox-active receptor can have a composition of formula I: wherein the variables L, R, R′, n and X − are described herein.

1 . A composition comprising:
 boronic acid-based synthetic redox-active receptors that can electrochemically sense a target analyte in a sample solution, and   a salt selected from the group consisting of:   
       
         
           
           
               
               
           
         
       
       where:
 X- is an anion; 
 R and R′ are independently —(CH 2 ) p-R   1 ; 
 R 1  is C 1 -C 6  alkyl-B(OR 2 )(OR 3 ), aryl-B(OR 2 )(OR 3 ), heteroaryl-B(OR 2 )(OR 3 ), or heterocyclyl-B(OR 2 )(OR 3 ); 
 R 2  and R 3  are independently H, C 1 -C 6  alkyl or R 2  and R 3  can combine with the B atom to form a ring system; 
 L and L′ are independently H, halogen, OH, CN, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkylthio, arylthio, alkoxy, aryloxy, -COOR 4 , NH 2 , —C(O)N(H)—(CH 2 ) p —N(H)C(O)—R 4 , —C(O)NH(R 4 ), or —N(H)C(P)R 4 ; 
 R 4  is independently at each occurrence H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, aryl, heteroaryl, heterocyclyl, or cycloalkyl; 
 n is 2, 3, 4, 5, or 6; and 
 p is 0, 1, 2, 3, 4, 5, or 6. 
 
     
     
         2 . The composition of  claim 1 , wherein each anion is selected from the group consisting of Br − , CI − , I − , F − , PF 6   − , sulfonate, mesylate, or triflate. 
     
     
         3 . The composition of  claim 1 , wherein p is 1. 
     
     
         4 . The composition of  claim 1 , wherein R 1  is aryl-B(OR 2 )(OR 3 ). 
     
     
         5 . The composition of  claim 1 , wherein R 1  is ortho-, meta-, or para-substituted phenylboronic acid, nitrophenylboronic acid, fluorophenylboronic acid, methoxyphenylboronic acid, aminophenylboronic acid, carboxyphenyboronic acid hydroxyphenylboronic acid, dimethylphenylboronic acid, bromophenylboronic acid or vinylboronic acid. 
     
     
         6 . The composition of  claim 1 , wherein L′ is —C(O)N(H)—(CH 2 ) p —N(H)C(O)—R 4 . 
     
     
         7 . The composition of  claim 6 , wherein L′ is —C(O)N(H)—(CH 2 ) 3 —N(H)C(O)—R 4  and R 4  is 2-propenyl. 
     
     
         8 . The composition of  claim 1 , wherein the salt of formula (I) has the structure: